Edible colouring materials

ABSTRACT

A edible composition comprising 8-amino-2-(azo-benzene-4sulphonic acid) 1-naphthol-3 6-disulphonic acid as a colouring material, named &#39;&#39;&#39;&#39;Red AB.

United States Patent Billington July 1, 1975 EDIBLE COLOURING MATERIALS[56] References Cited [75] Inventor: Arthur Ernest Billington, Watford,UNITED STATES PATENTS England 563,382 7/1896 Krecke et a]. 260/198 [73]Assigneez Beecham Group Limited, England 1,154,826 9/1915 Wulff et a1260/198 [22] Filed: Aug. 13, 1973 FOREIGN PATENTS OR APPLICATIONS858,183 1/1961 United Kingdom 260/198 pp 387,749 1,270,656 4/1972 UnitedKingdom 426/177 [30] Foreign Application Priority Data m y f LouisMonacell Aug 19, 1972 United Kingdom 38761/72 Asslsmm Emmmepl' Hume Oct.5, 1972 United Kingdom 45922/72 [57] ABSTRACT U-S- A edible compositionomprising 8 amin 2 (a o [51] Int. Cl A231 l/26 b -4- l h ni acid)l-naphth0l-3 6-disulphonic Fleld of Search I acid as a colouringmaterial named Red AB 9 Claims, N0 Drawings 1 2 EDIBLE COLOURINGMATERIALS which is 8-amino-2-(azo-benzene-4-sulphonic acid)-lnaphthol-3-disulphonic acid This invention relates to edible colouring materialsin Compound (Ill) has previously been used as a chemiparticular for usein beverage and cosmetic composil r t R Od d R, B b Kogyo K k tions. 5Zasshi 65 294 (1962); Chemical Abstracts 58 1450C A COmPQI-md Suitablefor inclusion into beverages as 1963)] and similar'compounds aredisclosed in British a colouring agent must have three requirements: itPat. No. 858,183 as dyestuffs for dyeing textile materimust have a goodtlnctol'ial P it must be g als. However compound (111) has not beenincorpocally accep bl d it must be Stable in the Presence rated as acolouring material in foodstuffs or cosmetics. of fruit acids and strongreducing agents such as sul- It has now been found that compound ([11)is in its phurous and ascorbic acids which are commonly pre own rightuseful as a colouring agent for foodstuffs or en! in Such compQsitlQnS-one red 3 which is compositions intended for contact with the mouth, formonly used for colouring beverages is colour index example lipstickcomposition. It has a higher tinctorial Consti ution O- 17200 Food Red mn y power than Red 10B and can therefore be used at lower known as Red10B which is the disodium salt of 8- 15 concentrations (by weight) toproduce the same effect amino-2-(phenylazo)-lnaphthol-3 6-disulphonicacid, thus resulting in greater safety in use as a food additive. offormula (1) Furthermore this compound is stable in acid conditions anddoes not produce Heinz bodies in the blood.

The present invention therefore provides an edible compositioncomprising 8-amino-2-(azo-benzene-4- sulphonic acid)-l-naphthol-36-disulphonic acid or an edible salt thereof together with an ediblediluent or carrier. We have named the compound of formula 111 Red AB"and it will be referred to as such throughout this specification.

From a second aspect the present invention provides an ediblecomposition comprising an edible diluent or carrier in which8-amino-2-(azo-benzene-4-sulphonic H we r one n r l f r of Red 10B is hacid)-l-naphthol-3 6-disulphonic acid or an edible salt it is now knownto produce an increase in the level of thereof is incorporated as such.Heinz bodies in the bloodstream when administered in B th termincorporated as such herein we mean high concentrations in the diet oftest animals. These that the compound itself is incorporated into thecomare bodies which appear in ageing red cells of blood. As position andnot a precursor or derivative of the coma result Red 108 is no longersuitable for universal und, whi h may be transformed to Red AB in situ.restricted use in food. A red colouring material which Red AB and/or itssalts may be used to colour all has been shown not be produce Heinzbodies is distypes of edible materials which are intended for conclosedin British Pat. No. 1,270,656 and is 8- sumption or contact with themouth. Suitable diluents acetamido-2-(azobenzene-4-sulphonic acid)-l andcarriers which may be coloured include, for examnaphth0l-3 6disulphO Cac d f o a 4O ple, beverages such as soft drinks, fruit ades, wines,

HO NH. COCH N N (II) Although the above patent discloses the u f cbeverage concentrates such as syrups powder concenpound 11 in a varietyof foodstuffs, it is particularly contra es or table s; ie ary ypefoods: ice creams shercerned with the colouring of sausage meats. Whilstit is ber'tS and ices; ice milk Products; bakery Products; stable insausage meat compositions, we have f nd, ing: confections such as boiledsweets and confection however that the compound (II) is undesirable foruse toppings, syr ps, jams and flavours, fruit gelatin desin beveragessuch as fruit Cordials or carbonated drinks Sens, Cake mlXeS; meatProducts; Cough y p and because the acetamide group i relatively t bl iother medicinal preparations intended for oral administhe acidconditions (pH 3.0-3.5) found in such prodtlation; dental PreparationsSuch as pastes Powders ucts; the compound is hydrolysed to the compou df foams; mouth washes and similar oral antiseptic liquids formula (III):and cosmetic formulations in particular lipsticks.

HO NH HSO N (III) Red AB and its saltsare particularly advantageous foruse in colouring carbonated and non-carbonated soft drinks and syrupconcentrates which may be made up to such drinks. In particular we havefound that Red AB produces an intense bluish red hue which isparticularly suitable for producing the colours customarily associatedwith dark-coloured fruits such as blackcurrant, black cherry,blackberry, blueberry etc.

Another composition in which the amount of organic colouring material issignificant is a lipstick composition. We have found that Red AB is alsouseful for incorporating into lipstick compositions.

Accordingly the invention further provides a lipstick compositioncomprising 8-amino-2-(azo-benzene-4- Comparison with Red lOB Thequantities of colouring agents required to produce the same colouringeffect for a blackcurrant syrup using (i) Red 108 and (ii) Red AB areshown below:

Thus a lower concentration of Red AB is sufficient to produce the sameintensity of colour as Red B.

. (i) Composition (ii) Composition using Red 108 using Red AB Red 108l33mg/kg Red AB lmg/kg Tartrazine 23mg/kg Tartrazine 23mg/kg Green S 2.7m /k Green S 2.7 mg/kg Total Colour 158 7mg/kg Total Colour 150 7 mg/kgsulphonic acid)-l-naphthol-3 6-disulphonic acid or an EXAMPLE 4 ediblesalt thereof together with a suitable carrier.

The salts which may be included in the compositions of this inventionmay be the mono-, di-, and/or tri-salts of Red AB. Suitable salts forinclusion into beverages include alkali-metal salts of Red AB,preferably the sodium salts. For lipstick compositions the compound ispreferably converted to an insoluble salt, for example, a barium orcalcium salt.

Red AB or its salts are incorporated in the material to be coloured inan amount required to attain the desired level of colouring. Preferredamounts of Red AB, for use in syrups cordials, ets., are 75 to 300mg/kg; and in ready to drink beverages from 1-75 mg/kg, preferably 25-50mg/kg.

Preferred amounts for use in lipstick compositions are from l-l0% byweight.

The invention is illustrated by the following examples:

EXAMPLE 1 Preparation of 8-amino-2-(azo-benzene-4-sulphonicacid)-l-naphthol-3 6-disulphonic acid Sulphanilic acid (l4.4g; 0.0833mole) and sodium carbonate (4.42g; 0.0416 mole) were dissolved in water(330 ml), cooled to 0 then added with stirring, to sodium nitrite(5.25g; 0.076 mole) in water (76ml) at 0. This mixture was added withstirring to 5N Hydrochloric acid (32 ml) at 0 then the resultantsuspension was added rapidly to a solution of 8-amino-lnaphthol-36-disulphonic acid, monosodium salt (g; 0.0839 mole) and sodiumhydroxide 10 g; 0.25 mole) in water (125 ml) at 0. The violet solutionwas stirred for 30 minutes then 5N Hydrochloric acid was added drop-wiseuntil pH 7.0 was achieved. The water was removed on a rotary evaporatorthen the resultant brittle solid was warmed, on a water bath, withethanol (750ml) and water (200ml) with occasional shaking for 2 hours.The deep violet solution was decanted then left in a refrigeratorovernight whereupon the dye precipitated. This was filtered off thendried at 68 in a vacuum oven. Yield =30.l5g. (76.9% based on sulphanilicacid).

EXAMPLE 2 A blackcurrant syrup was prepared having the followingcomposition:

A lipstick composition was prepared as follows:

Base Castor Oil 69.50

Cocoa Butter substitute l4.00 Candelilla Wax 9.00 Beeswax 6.00CamaubaWax l 5( l00.00 Base 95% 8-amino-2-(azo-benzene-4-sulphonicacid)-l-naphthol-3 -disulphonic acid 5'71 1 claim:

1. An food composition comprising 8-amino-2-(azobenzene-4-sulphonicacid)-1-naphthol-3 6-disulphonic acid or an edible salt thereof togetherwith foodstuff.

2. A composition according to claim 1 wherein the foodstuff is abeverage.

3. A composition according to claim 2 wherein the beverage is acarbonated or non-carbonated soft drink.

4. A composition according to claim 1 wherein the foodstuff is a syrupconcentrate which may be made up to a soft drink.

5. A composition according to claim 2 wherein the beverage contains thesalt and said salt is the sodium salt of8-amino-2-(azo-benzene-4-sulphonic acid)-lnaphthol-3 o-disulphonic acid.

6. A composition according to claim 3 in which the amount of8-amino-2-(azo-benzene-4-sulphonic acid)- l-naphthol-3,6-disulphonicacid or edible salt thereof is 1-75 mg/kg.

7. A composition according to claim 6 wherein the amount is 25-50 mg/kg.

8. A composition according to claim 4 wherein the amount of8-amino-2-(azo-benzene-4-sulphonic acid)- l-naphthol-3,-disulphonic acidor edible salt thereof is -300 mg/kg.

9. A method of colouring food compositions which comprises incorporatinginto the composition a colouring amount of8-amino-2-(azo-benzene-4-sulphonic acid)-l-naphthol-3, 6-disulphonicacid, or an edible salt thereof. 7

1. AN FOOD COMPOSITION COMPRISING 8-AMINO-2-(AZO-BENZENE-4-SULPHONICACCID)-1-NAPHTHOL-3 6-DISULPHONIC ACID OR AN EDIBLE SALT THEREOFTOGETHER WITH FOODSTUFF.
 2. A composition according to claim 1 whereinthe foodstuff is a beverage.
 3. A composition according to claim 2wherein the beverage is a carbonated or non-carbonated soft drink.
 4. Acomposition according to claim 1 wherein the foodstuff is a syrupconcentrate which may be made up to a soft drink.
 5. A compositionaccording to claim 2 wherein the beverage contains the salt and saidsalt is the sodium salt of 8-amino-2-(azo-benzene-4-sulphonicacid)-1-naphthol-3 6-disulphonic acid.
 6. A composition according toclaim 3 in which the amount of 8-amino-2-(azo-benzene-4-sulphonicacid)-1-naphthol-3,6-disulphonic acid or edible salt thereof is 1-75mg/kg.
 7. A composition according to claim 6 wherein the amount is 25-50mg/kg.
 8. A composition according to claim 4 wherein the amount of8-amino-2-(azo-benzene-4-sulphonic acid)-1-naphthol-3,6-disulphonic acidor edible salt thereof is 75-300 mg/kg.
 9. A method of colouring foodcompositions which comprises incorporating into the composition acolouring amount of 8-amino-2-(azo-benzene-4-sulphonicacid)-1-naphthol-3, 6-disulphonic acid, or an edible salt thereof.